Chloroacetyl chloride → 2-Chloro-2',5'-dimethoxyacetanilide

HRID 1190776Notes

Reaction equation

HRID 1190776 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH2:5].C(=O)(O)[O-].[Na+].[Cl:17][CH2:18][C:19](Cl)=[O:20]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:17][CH2:18][C:19]([NH:5][C:4]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1])=[O:20]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 76132,5-DimethoxyanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 309612-Chloro-2',5'-dimethoxyacetanilide

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

2,5-dimethoxyaniline (20 g., 130.56 mmol) was suspended in water (300 ml) followed by the addition of sodium bicarbonate (13.4 g., 156.6 mmol)) and tetrabutylammonium bromide (catalytic amount). To the mixture was added chloroacetyl chloride (12.4 ml, 156.6 mmol) dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 h. The solid suspension was filtered off to yield pure 46. Yield=23.6 g (79%). 1H NMR: 9.46 (1H), 7.68 (1H, d, J=2.96 Hz), 6.96 (1H, d, J=8.96 Hz), 6.43 (1H, dd, J=8.95 and 3.06 Hz), 4.37 (s, 2H), 3.79 (s, 3H), 3.67 (s, 3H). 13C NMR: 43.3, 55.9, 56.2, 106.0, 111.0, 127.4, 127.7, 142.7, 154.0, 163.8. ES-HRMS [M+H]+ 230.0509. Calcd for (C10H13NO3): 230.0578.

Workup

  1. filtrationThe solid suspension was filtered off
  2. customto yield pure 46

Sources & evidence

ORD record
ord-45d25c0a42a442218481a1bbff829f3a
Source dataset
uspto-grants-2014_03
Patent number
US08679776B2

Reaction notes

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